My husband and I purchased a dual-strap on harness, such that there is a spot for a dildo as well as a lower hole for a biological penis. I believe the intended purpose is for double penetration, that’s what we got it for and what it advertises, but I do not see why the dildo couldn’t be the main event. It’s even on Amazon. It’s the “Spare Parts Deuce (double strap) harness”.

Another recommendation:

A cock sheath may work in this scenario, especially if he can get semi-hard. Oxballs has some nice options. They also have a product called a "double fucker." It's a dildo you strap-on above your cock for double-penetration. It might work as well!

And:

Spare Parts harnesses work great for all genders! I have one that both I and my partner with opposite bits would use. We also have a pretty large size difference between both of us and it fits us both. Machine washable too!

Your advice to the older gentlemen seeking advice re: relationships with younger men was totally tinged with a weird shade of shame. I don't think he is a creep at all... but you? I'm not sure I can say the same. Then your advice for the cuckold scenario that originated in THE WORK PLACE. I know you haven't probably had a real job since you worked at that Blockbuster in Minnesota (yes, I so remember YOU — angry, closeted, misogynistic), but THE WORK PLACE is not the place for this type of scene to develop. If it goes badly, a distinct possibility, and starts to affect their work relationship AND HR gets a whiff of it — both these dudes will be shown the door. So... yeah. Really disappointed in you.

If you read shame into my response to the older gentleman with the younger lover, that's on you. I have no issue with sexual and/or romantic relationships with large age gaps — if I did, I wouldn't have created the Campsite Rule, now would I? The LW asked if he was a creep, and I acknowledged that while the age gap would creep some people out, "that doesn't mean you're a creep." As for the cuckold scenario in the same column: yes, the LW met this couple — the male half — though work. But as the LW indicated, they are equals. We should encourage people to be thoughtful about initiating relationships with workmates (particularly subordinates, although some of those have worked out pretty well); and, yes, we want the bar to be higher and for people to be cautious about approaching coworkers they might be attracted to and, yes, we all want the consequences for sexual harassment in the workplace to be swift and severe. But telling people they can NEVER EVER sleep with someone they met at work isn't just unrealistic (while the numbers are falling and most couples meet online now, 10% of couples met through work), making workplace relationships/hookups absolutely taboo will make them more alluring, not less, by dint of being forbidden.

And finally... I worked at an independent video store in Madison, Wisconsin, and I'd already been out of the closet for a decade before I got that job. So either your memory is going or you're thinking about some other video store clerk.

I was surprised that you didn’t address the important issue of sexual involvement with coworkers/bosses/spouses in your reply to HISBULL. It’s generally not a good idea to get sexually involved with coworkers because of the risk to one’s job. How can HISBULL be sure that his coworker doesn’t want to compromise him or set him up for blackmail or accusations of sexual harassment or other conduct that’s forbidden in the employees’ manual or contract? Having sex with a coworker’s spouse, for whatever reason, seems to me to fall into the “too close for comfort” category.

I should've addressed it, particularly at this cultural moment. I actually think "generally not a good idea" is a good standard to apply to workplace relationships — it's generally not a good idea, people should think long and hard before asking a coworker out/hitting on coworker or taking a coworker up on his offer to, say, fuck his wife while he watches. (Better yet: think about it long and not hard.)

More and more young women (and some men) and becoming Sugar Babies in order to go (pay for) college without burdening themselves with crippling debt. I not entirely sure if this qualifies as sex work since they essentially become mistresses. I (and they) find this as a pragmatic solution to the problem of the high cost of college. It is unlikely that they are virgins and far superior to what Anna Nicole Smith and Melania did when they married Billionaires (an octogenarian and an odious, loathsome troll [who may or may not be a billionaire] respectively. Anna Nicole got the better deal even though she never received any money from her husband's family or estate. She was married for only 13 months and reportedly never had sex with husband).

And:

As long as you treat yourself and others with respect and dignity, sugar baby/daddy can be a great situation for people. I transitioned from stripping to being a sugar baby in my early twenties and it was a great time in my life. I went on vacations, had some incredible meals, learned about wine, bought the car I still drive from him for $400, and he was a good friend to me. His wife had died of ovarian cancer and he had survived prostate cancer. There was nothing abusive about it.

I'm surprised the expert you contacted hadn't heard of the most internet famous example of the worm thing. Blowfly Girl. You can find her blog, or not, with a couple clicks from a google search. Gets far more extreme than letter writer. Would have expected at least one comment person on a column about weird sex shit to know about that. Pardon the unrelated email, since I don't Twitter these days I grabbed whatever email gmail kicked up when I hit the page.

Please note: I do NOT recommend clicking your way toward Blowfly Girl.

Bloody ejaculate may also be the result of a recent prostate biopsy. As a prostate cancer survivor I had two such procedures before eventually undergoing a prostatectomy. After each biopsy my ejaculate was very bloody/dark brown. This lasted for about 2-3 weeks. This can be verified by any urologist.

And:

I can add some information to your recent topic on the topic of "blood in the condom." Blood mixed with semen can be the result of having received a biopsy to test for the presence of prostate cancer.

In my case, about 18 months ago (I was 55) my normal physical blood tests showed elevated Prostate Specific Antigen (PSA) levels. This resulted in a visit with an urologist, who obtained prostate tissue samples with what was called a 'transrectal orbital probe' inserted via the rectum. The procedure was relatively painless, a series of 10 or so slight stapler-like pricks into the prostate gland, which does not have any significant nerves.

I was told, in a rather minor offhand way, that afterwards blood might appear in my rectum, urine, or semen. A few days later I masturbated, and was glad I was by myself, as it is truly unusual to see a stream of bright red semen streaming from one's penis. Perhaps there are some X-rated porno horror movies which depict such a scene, but if so, those were films I never saw, so it certainly took me by surprise. The bright red semen continued with my next few masturbation sessions, then the color shifted to a more rusty darker brown (like coagulated blood) that slowly grew more and more faint. One month later, my semen was back to normal. I was fortunate that my biopsy tests came back negative, and 6 months later my PSA levels were back to normal.

In hindsight, I wish the health staff would have been more forthcoming with the possible effects of the biopsy, but evidently the term 'You may cum blood' is not within the bounds of accepted medical lexicon to provide to one's patients.